Besifloxacin HCl is a potent and fourth-generation fluoroquinolone antibiotic. Besifloxacin is a novel 8-chloro-fluoroquinolone agent with potent, bactericidal activity against prevalent and drug-resistant pathogens.besifloxacin is the most potent agent tested against gram-positive pathogens and anaerobes and is generally equivalent to comparator fluoroquinolones in activity against most gram-negative pathogens. Besifloxacin demonstrates potent, broad-spectrum activity, which is particularly notable against gram-positive and gram-negative isolates that are resistant to other fluoroquinolones and classes of antibacterial agents.
Physicochemical Properties
| Molecular Formula | C19H21CLFN3O3.HCL |
| Molecular Weight | 430.3 |
| Exact Mass | 429.102 |
| Elemental Analysis | C, 53.03; H, 5.15; Cl, 16.48; F, 4.42; N, 9.77; O, 11.15 |
| CAS # | 405165-61-9 |
| Related CAS # | Besifloxacin;141388-76-3 |
| PubChem CID | 10224595 |
| Appearance | solid powder |
| Boiling Point | 607ºC at 760 mmHg |
| Melting Point | >210ºC (dec.) |
| Flash Point | 320.9ºC |
| LogP | 4.712 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 28 |
| Complexity | 656 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | ClC1C(=C(C([H])=C2C(C(C(=O)O[H])=C([H])N(C2=1)C1([H])C([H])([H])C1([H])[H])=O)F)N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(C1([H])[H])N([H])[H].Cl[H] |
| InChi Key | PMQBICKXAAKXAY-HNCPQSOCSA-N |
| InChi Code | InChI=1S/C19H21ClFN3O3.ClH/c20-15-16-12(18(25)13(19(26)27)9-24(16)11-4-5-11)7-14(21)17(15)23-6-2-1-3-10(22)8-23;/h7,9-11H,1-6,8,22H2,(H,26,27);1H/t10-;/m1./s1 |
| Chemical Name | (+)-7-[(3R)-3-aminohexahydro-1H-azepin-1-yl]-8-chloro-1- cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride. |
| Synonyms | BOL 303224a; BOL-303224a; BOL303224a; BOL-303224-A; SS734; SS-734; SS 734; Besifloxacin HCl; Besivance. |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
Besifloxacin was the most potent agent tested against gram-positive pathogens and anaerobes and was generally equivalent to comparator fluoroquinolones in activity against most gram-negative pathogens. Besifloxacin demonstrated potent, broad-spectrum activity, which was particularly notable against gram-positive and gram-negative isolates that were resistant to other fluoroquinolones and classes of antibacterial agents.[2] Activity of besifloxacin against gram-positive aerobes. Against Enterococcus faecalis and E. faecium, including vancomycin-resistant enterococci, besifloxacin was more potent than the comparator fluoroquinolones, as well as azithromycin, vancomycin, and tobramycin . Besifloxacin further demonstrated excellent activity against Listeria monocytogenes, similar to that of tobramycin and penicillin and better than that observed with comparator fluoroquinolones.[2] Activity of besifloxacin against gram-negative aerobes. For three Acinetobacter spp. (which included 16 to 64% non-ciprofloxacin-susceptible isolates), the besifloxacin MIC90s (16 to 32 μg/ml) were similar to or lower than the ciprofloxacin values, and for two of these species, the besifloxacin MIC90s were two- to fourfold higher than the corresponding values for levofloxacin and moxifloxacin .[2] Activity of besifloxacin against gram-positive and -negative anaerobes.[2] For five of the six anaerobic species, besifloxacin MIC90s were equal to or lower than those for the most active comparators, including clindamycin, metronidazole, and the other fluoroquinolones (Table 3). Against Propionibacterium acnes, the most active agent was clindamycin, with a 0.12 μg/ml MIC90, while the corresponding besifloxacin and moxifloxacin values were twofold higher. Overall, besifloxacin and moxifloxacin were the most active agents tested against anaerobic bacteria.[2] |
| References | Ophthalmology.2009 Sep;116(9):1615-1623.e1.;Antimicrob Agents Chemother.2009 Aug;53(8):3552-60. |
| Additional Infomation |
Besifloxacin Hydrochloride is the hydrochloride salt form of besifloxacin, a synthetic fourth-generation fluoroquinolone antibiotic, with broad spectrum antibacterial activity. Upon administration, besifloxacin targets, binds to and inhibits both bacterial DNA gyrase, an enzyme essential for DNA replication, transcription and repair of bacterial DNA, and bacterial topoisomerase IV, an enzyme required for partitioning of the chromosomal DNA during bacterial cell division. This inhibits DNA replication, transcription, and repair and cell division. See also: Besifloxacin (has active moiety). |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~1 mg/mL (~2.32 mM) H2O : ~0.1 mg/mL (~0.23 mM) Ethanol : < 1 mg/mL |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3240 mL | 11.6198 mL | 23.2396 mL | |
| 5 mM | 0.4648 mL | 2.3240 mL | 4.6479 mL | |
| 10 mM | 0.2324 mL | 1.1620 mL | 2.3240 mL |